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Poughkeepsie Vacation Rentals

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50 rentals in Poughkeepsie.
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The Queen City Cottage, vacation rental in Poughkeepsie

The Queen City Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Brick House -Hudson Valley, vacation rental in Poughkeepsie

Charming Brick House -Hudson Valley

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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HUDSON VALLEY! Spectacular Space On a Scenic Mountain~ tons of Family Activities, vacation rental in Poughkeepsie

HUDSON VALLEY! Spectacular Space On a Scenic Mountain~ tons of Family Activities

5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Renovated  Cottage in the Heart of Hudson Valley close to Walkway Over Hudson, vacation rental in Poughkeepsie

Renovated Cottage in the Heart of Hudson Valley close to Walkway Over Hudson

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Ulster Park Haven with Magnificent Hudson River Views, vacation rental in Poughkeepsie

Waterfront Ulster Park Haven with Magnificent Hudson River Views

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hudson valley getaway, vacation rental in Poughkeepsie

Hudson valley getaway

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Hudson Valley 3 Bedroom Home, vacation rental in Poughkeepsie

Newly Renovated Hudson Valley 3 Bedroom Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Valley vacation house, vacation rental in Poughkeepsie

Hudson Valley vacation house

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Historic Hudson Valley Farmhouse | Close to wineries, hiking, & museums, vacation rental in Poughkeepsie

Charming Historic Hudson Valley Farmhouse | Close to wineries, hiking, & museums

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska, vacation rental in Poughkeepsie

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stylish and modern house in the quaint town of Millbrook., vacation rental in Poughkeepsie

Stylish and modern house in the quaint town of Millbrook.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views., vacation rental in Poughkeepsie

Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views.

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Renovated Schoolhouse - Hudson Valley Getaway, vacation rental in Poughkeepsie

Renovated Schoolhouse - Hudson Valley Getaway

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Ridge View Walk-up - Close to Mohonk Preserve, Minnewaska, New Paltz & Gardiner, vacation rental in Poughkeepsie

Ridge View Walk-up - Close to Mohonk Preserve, Minnewaska, New Paltz & Gardiner

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Orchard Keeper's Private Apt. - Entire Second Floor of 1873 Marlboro Farmhouse, vacation rental in Poughkeepsie

Orchard Keeper's Private Apt. - Entire Second Floor of 1873 Marlboro Farmhouse

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Country Oasis, with pool, pond on a lush 16 acres, vacation rental in Poughkeepsie

Gorgeous Country Oasis, with pool, pond on a lush 16 acres

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular Kitchen, 6 Bedrooms, On 20 Acre Estate With Heated In-Ground Pool, vacation rental in Poughkeepsie

Spectacular Kitchen, 6 Bedrooms, On 20 Acre Estate With Heated In-Ground Pool

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Dutchess County 5 star Luxury Estate . 10 minutes from Rhinebeck, vacation rental in Poughkeepsie

Dutchess County 5 star Luxury Estate . 10 minutes from Rhinebeck

8 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Cozy And Inviting Nestled In The Heart Of Ny Apple Mecca. Easy 5 Min. To Village, vacation rental in Poughkeepsie

Cozy And Inviting Nestled In The Heart Of Ny Apple Mecca. Easy 5 Min. To Village

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront Cottage, Hudson Valley NY, vacation rental in Poughkeepsie

Lakefront Cottage, Hudson Valley NY

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Earth Berm House at Terra Casa Retreat Center, vacation rental in Poughkeepsie

Earth Berm House at Terra Casa Retreat Center

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private King Bed w/Bath in SHARED Charming House, good for business travelers, vacation rental in Poughkeepsie

Private King Bed w/Bath in SHARED Charming House, good for business travelers

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Renee's Get-Away New Paltz, vacation rental in Poughkeepsie

Renee's Get-Away New Paltz

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Secluded Country Getaway, vacation rental in Poughkeepsie

Secluded Country Getaway

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff, vacation rental in Poughkeepsie

Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff

4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Millbrook Country Dream! Tennis/Swim/Play, vacation rental in Poughkeepsie

Millbrook Country Dream! Tennis/Swim/Play

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Unique Hudson Riverfront Home & Pool, vacation rental in Poughkeepsie

Unique Hudson Riverfront Home & Pool

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Phillie's Country Comfort Space   -, vacation rental in Poughkeepsie

Phillie's Country Comfort Space -

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Black Creek Bed and Breakfast, vacation rental in Poughkeepsie

Black Creek Bed and Breakfast

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Black Creek Bed and Breakfast (Reclaimed Room w/Shared Bathroom), vacation rental in Poughkeepsie

Black Creek Bed and Breakfast (Reclaimed Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Black Creek Bed and Breakfast (Zen Room w/Shared Bathroom), vacation rental in Poughkeepsie

Black Creek Bed and Breakfast (Zen Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Black Creek Bed and Breakfast (Arbor Room w/Shared Bathroom), vacation rental in Poughkeepsie

Black Creek Bed and Breakfast (Arbor Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Black Creek Bed and Breakfast (Paris Room w/Shared Bathroom), vacation rental in Poughkeepsie

Black Creek Bed and Breakfast (Paris Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gatehouse Gardens, vacation rental in Poughkeepsie

Gatehouse Gardens

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Grotto View at Stone Mountain Farm, vacation rental in Poughkeepsie

Tentrr Signature Site - Grotto View at Stone Mountain Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Creekside Solitude, vacation rental in Poughkeepsie

Tentrr Signature Site - Creekside Solitude

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Kamp Kimberg North, vacation rental in Poughkeepsie

Tentrr Signature Site - Kamp Kimberg North

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Mini Yosemite in the Hudson Valley, vacation rental in Poughkeepsie

Tentrr Signature Site - Mini Yosemite in the Hudson Valley

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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5 Bedroom 20 Acre Country Estate with a Pool in Hudson Valley, vacation rental in Poughkeepsie

5 Bedroom 20 Acre Country Estate with a Pool in Hudson Valley

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Hudson Valley Retreat: Huge Deck w/ views, 7 acres, 90 min from NYC, vacation rental in Poughkeepsie

Stunning Hudson Valley Retreat: Huge Deck w/ views, 7 acres, 90 min from NYC

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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5 Bedroom Rustic Country Home, vacation rental in Poughkeepsie

5 Bedroom Rustic Country Home

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Reservoir Retreat, vacation rental in Poughkeepsie

Tentrr Signature Site - Reservoir Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Rifton Farm Hidden Forest, vacation rental in Poughkeepsie

Tentrr Signature Site - Rifton Farm Hidden Forest

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Honeybug Hill near Omega, vacation rental in Poughkeepsie

Tentrr Signature Site - Honeybug Hill near Omega

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Midcentury Modern House with Stunning Views, vacation rental in Poughkeepsie

Midcentury Modern House with Stunning Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Hudson Valley 1880 Carriage House with FIRE PLACE, vacation rental in Poughkeepsie

Cozy Hudson Valley 1880 Carriage House with FIRE PLACE

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Famous Liberty View Farm, vacation rental in Poughkeepsie

Famous Liberty View Farm

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Modern, Luxury Vintage CAMPER with Swimming Pool in the Hudson Valley, vacation rental in Poughkeepsie

Modern, Luxury Vintage CAMPER with Swimming Pool in the Hudson Valley

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gorgeous Hudson Valley Villa, vacation rental in Poughkeepsie

Gorgeous Hudson Valley Villa

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cozy cottage in Hudson Valley-Dog friendly, vacation rental in Poughkeepsie

Cozy cottage in Hudson Valley-Dog friendly

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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